


Are You Gonna Kiss Me or Not?

by CeliPuff



Category: Supernatural
Genre: Bisexual Dean Winchester, Castiel Has a Crush on Dean Winchester, Castiel/Dean Winchester First Kiss, Castiel/Dean Winchester One Shot, Dean Winchester Has a Crush on Castiel, Dean Winchester Needs to Use Actual Words, Fluff, Gay Castiel (Supernatural), M/M, Mutual Pining, POV Castiel (Supernatural)
Language: English
Status: Completed
Published: 2019-12-23
Updated: 2019-12-23
Packaged: 2021-02-26 01:14:27
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,822
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21915058
Author URL: https://archiveofourown.org/users/CeliPuff/pseuds/CeliPuff
Summary: Dean kissed a boy and he liked it.
Relationships: Castiel/Dean Winchester
Comments: 13
Kudos: 108





	Are You Gonna Kiss Me or Not?

**Author's Note:**

  * For [Winchesterlovr0508](https://archiveofourown.org/users/Winchesterlovr0508/gifts).



> Another Christmas gift for my beautiful Gryffindor ❤️

Where do I even begin… 

A little over a year ago, I met a man named Dean Winchester. 

Yeah... let’s start there. Dean was fucking beautiful. He was slightly taller than me, with these _out of this world_ green eyes and sandy brown hair. He had about sixty five freckles on his nose, and yes, I tried to count them but he never stays still. 

I could stare at him _all_ day and his personality could make the strongest fall to their knees. He’s fun, charismatic, flirty and completely fucking _clueless._

I had been pining over him since the day we met. Except, of course, he was “straight”. _Keep those air quotes in mind._

I quickly became his wing man, which sucked. No other word to describe it. It _sucked!_ We were friends for _twelve_ whole months before he realized I was even gay, _that_ is his level of cluelessness. 

Dean randomly turned to me one night when we were out at a bar. “Why do you always let me have all the chicks?” 

It was a particularly slow night and the bar was full of dudes, I sure wasn’t complaining but Dean’s question completely distracted me.

“What?!” I asked, unable to hide the shock in my voice. “Why would I want them?” This sounds dumb now, but at the time, I had no idea what he was asking. _Everyone_ knew I was gay. 

He frowned, just as confused as I was. This wasn’t either of our best moments. “Do you need details? I know you’re _not_ a virgin Cas. Why else take random chicks home?” 

“I never take random chicks home. Why-” and that was when it hit me. He had no fucking clue! Dean was so wrapped up in his own bullshit he didn’t notice his _roommate_ was gay. 

I came out when I was in the ninth grade. A girl named Meg kissed me... ugh. So naturally, I pulled away and yelled “Sorry I’m gay!” Then took off running home. Yes, you read that right, I _yelled_ it. It was quite embarrassing but a relief to say it out loud, plus, it got her to stay away so there’s that. 

“Dean are you serious?!” I asked, “We’ve lived together for a year!” 

Still clueless, “Thanks Captain Obvious!” Dean took a drink of his beer, frowning.

“Dean I am very, _very_ gay.” This was gold, I will _never_ forget the look on his face.

Dean Winchester was speechless. 

“You’re… Um... shit. Congrats? I don’t know what people say here.” Embarrassed Dean is _adorable_ , let me just throw that out there.

“Normally when a man comes out to another man, it is customary to kiss them. You know, to show you aren’t a homophobe.” Biting back this laugh was fucking _hard!_

Except it backfired when Dean slammed back his beer and held out his arms. “Alright. Let’s do this.” 

It was my turn to be embarrassed.

All that came out of my mouth was. “Seriously?” 

“Are you gonna kiss me or not?” He asked abrasively. 

“Not.” It was _this_ moment I knew Dean had definitely thought about kissing me before. The look in his eyes said so much, even while his mouth said _so_ little. 

“Oh.” 

There was an awkward three minutes before my brain started working again, “Dean I was fucking with you.”

“Duh. I was just calling your bluff.” He lied, while ordering another drink, this time slamming it back. Dean was upset and about to do some annoying _Dean thing_ to prove he doesn’t care, because he so _obviously_ cares. 

“Save my seat, there has to be a decent chick somewhere.” Dean got up and went _hunting_ before I could say anything else. 

All I could do was roll my eyes. Classic Dean. Why talk about feelings when we could be compensating said feelings with random flings? 

After another drink, I assumed Dean found someone and went on my own hunt. I was annoyed, I normally wouldn’t do this, especially after… whatever _that_ was with Dean.

It didn’t take long to find someone willing. Now, I know I’m no Dean Winchester but getting laid has never been hard for me. Apparently, dark hair and blue eyes is a “thing” for people. Personally, I don’t get it, but you also won’t hear me complaining. I just prefer green eyes. 

I leaned against the bar and looked around, instantly spotting a shorter man that was staring at me in _that_ way. You know, the way gays look at each other when we’re basically asking for a quicky in the bathroom. 

Gaydar is real people and no, you can’t buy it in stores. 

I waited for him to make eye contact with me, then gave him a quick head nod and it was a done deal. I made my way to the bathroom after I saw the man slip away from his friends and head that way. 

Except when I opened it, Dean was in there washing his hands absentmindedly. He was completely lost in thought and I actually wondered how long he had been washing his hands. Before I could ask Dean if he was okay, the shorter man was walking up. “Hey there handsome, I was hoping to see you in here.”

Dean’s head shot up and he looked at us both. You could see the moment he realized what was happening. 

I’m sure I had that deer in the headlights look because Dean frowned. “Are you two about to hook up in here?” 

The shorter man spoke, apparently I didn’t know english anymore. “Well I was hoping. You’re not so bad yourself handsome, I’m okay with three but we should probably find a different location for that.” 

I laughed. _Loudly_. Both of them were completely confused at why I laughed so loud, okay all three of us were. But Dean’s face was _priceless_. I could imagine all the thoughts going through his mind, _did I just get invited to a gay threesome, a gay threesome with Cas?!_ Dean was borderlining panic mode.

I had to turn on my brain and step up for my friend. “Dean here is straight. I know, I know, we’re all disappointed in that fact.” I touched the man’s cheek. “He’s also my ride home, so we’re going to have to take a raincheck alright sweetheart?” I licked my lips, staring into the man’s hazel eyes. I really _would_ have had fun with this one. 

The man made a pouty face and kissed my cheek. “With that voice? That raincheck is good any time, anywhere.” He winked and left the bathroom.

I finally looked back at Dean and his mouth hung open. He shut it, opened it to say something and then closed it again. Did my voice just affect him too? If this wasn’t my best friend _and_ roommate, I would have stepped into Dean’s space and made him squirm. It was also the moment I realized Dean was _definitely_ a bottom. 

He enjoyed being submissive, I’ve seen how he is with women and he’s told me how much he likes it when they boss him around and ride him. If only he’d let _me_ ride him. 

I’m primarily a top, but I _would_ bottom for Dean Winchester. Anything to get him out of the fucking closet. 

“Ready to go?” Felt like a safe question to ask when I realized we were still standing there staring. 

“Uh, yeah. Let’s go.” And so it seemed, Dean _didn’t_ have a conquest of the night waiting for him. 

The drive home was awkward. Unfortunately. But Dean seemed to be having some internal battle going on. When we walked into our three bedroom rental, he finally spoke up. “Sorry if I cock blocked you back there. I literally just found out my best friend was gay and then ran into him about to get it on in the bathroom with a dude.”

“You did cock block me, but it’s okay. You seemed like you wanted to head home. No amount of ass is more important than your comfort.” I stated matter of factly. 

Dean actually looked surprised. “How many times have I left you uncomfortable somewhere so I could get laid in the backseat of Baby?”

He had a point. “Too many times.” I sighed. 

“Shit man, I’m sorry.” He walked closer. “I never thought of it that way.”

“I know. Don’t worry about it Dean.” I shrugged, unsure of what else to say. 

“No really, I’m sorry. I won’t do that shit anymore, okay?” This was a different side of Dean and frankly much more intimate than I’ve ever seen him. Even with his ex girlfriend Lisa, who he broke up with after I lived here for a couple months.

“Okay. Dean are you okay?” I tilted my head, trying to read him.

He huffed a laugh and looked down. “Yeah, I’m okay Cas. Can I ask you a question?” 

I nodded, “Of course.” 

“How’d you know you liked dudes? Like, did you just know? Or did you just have to try it one day and see how you felt?” 

Not at _all_ what I expected. 

I couldn’t help but smile, “I just knew. I think we all know, we just decide when we come to terms with it. Why?” I knew why.

Dean shrugged, already returning to his carefree self. It was now or never. 

“Dean.” I took a step forward. “Talk to me.” I needed him to say it.

“I don’t know Cas. I was just curious.” His voice was sharp but he deflated in front of me the moment he allowed our eyes to lock. “I wanted to know… if like… like if we just know. I’ve been thinking about it a lot, even before tonight. What it would be like and stuff. But I was curious if those are just thoughts and if I tried it, is there still a possibility I wouldn’t actually like it.” Dean was rambling. But I still needed more. 

“Thinking about _it?_ It as in, what it would be like with a man?” 

Or what it would be like with _me_. I was too chicken shit to ask.

“Well… yeah. But more importantly… with… you.” Dean eyed me, the worry written on every inch of his body. He didn’t want to lose me as a friend but he wanted something _more_ with me. 

“Me too.” I said, before I could think of a better response. 

Dean smiled his award winning smile, the one that should be on magazines. “Well, glad that’s out there.” He scratched the back of his neck. “What now?” He asked, nervously.

“Well, are you gonna kiss me or not?” Okay, I know this was cheesy, but it fucking worked.

Dean laughed, blushed, and shook his head yes. 

Who kissed who first? Who knows. But it was the best kiss of my life.

We had no idea it was the beginning of our _forever._


End file.
